Application of Indolyl Ynones in the Construction of Chiral Carbazoles and Pyrroloindolines by Organo and Metal Sequential Catalysis.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-13 Epub Date: 2025-06-04 DOI:10.1021/acs.orglett.5c01900

Qing-Qing Li, Qian-Jun Lin, Yi Gao, Wen-Jing Xiao, Xue-Qing Song, Longfei Li, Wan Li, Ya-Li Song, Zhi-Hao You

引用次数: 0

Abstract

The enantioselective synthesis of carbazoles and pyrroloindolines has been achieved through organo-catalyzed and metal sequential-catalyzed one-pot reactions of indolyl ynones. Chiral carbazoles can be synthesized from the reactions of indolyl ynones and nitroolefins through an organo-catalyzed Michael addition followed by a gold-catalyzed Friedel-Crafts reaction/aromatization process. The reactions of indolyl ynones and N-tosyl imines lead to the generation of pyrroloindolines via an organo-catalyzed Mannich reaction and a silver-catalyzed dearomatizing spirocyclization/N,N-acetalization cascade reaction.

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吲哚酮在手性咔唑和吡咯啉的有机和金属顺序催化合成中的应用。

通过吲哚酮的有机催化和金属顺序催化一锅反应，实现了咔唑和吡咯啉的对映选择性合成。手性咔唑是由吲哚酮和硝基烯烃通过有机催化的Michael加成反应和金催化的Friedel-Crafts反应/芳构化反应合成的。吲哚酮和N-甲酰基亚胺通过有机催化的曼尼希反应和银催化的去芳化螺旋环化/N，N-乙酰化级联反应生成吡咯啉。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.